Synthesis and anticonvulsant activity of novel and potent 2,3- benzodiazepine AMPA/kainate receptor antagonists

Journal of Medicinal Chemistry

Volumn 42, Issue 21, 1999, Pages 4414-4421

  Grasso, Silvana ^a   De Sarro, Giovambattista ^b   De Sarro, Angela ^b   Micale, Nicola ^b   Zappala, Maria ^b   Puia, Giulia ^b   Baraldi, Mario ^b   De Micheli, Carlo ^b  

^a UNIVERSITY OF MESSINA   (Italy)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMPA RECEPTOR ANTAGONIST; ANTICONVULSIVE AGENT; BENZODIAZEPINE DERIVATIVE; KAINIC ACID RECEPTOR ANTAGONIST;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CELL CULTURE; DRUG EFFECT; DRUG POTENCY; DRUG SYNTHESIS; INTRAPERITONEAL DRUG ADMINISTRATION; MOUSE; NERVE CELL; NONHUMAN; PATCH CLAMP;

ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; ANIMALS; ANTICONVULSANTS; CELLS, CULTURED; CONVULSANTS; DRUG EVALUATION, PRECLINICAL; ELECTROSHOCK; EXCITATORY AMINO ACID ANTAGONISTS; KAINIC ACID; MALE; MICE; MICE, INBRED DBA; MOTOR ACTIVITY; NEURONS; PATCH-CLAMP TECHNIQUES; PENTYLENETETRAZOLE; PYRROLIDINONES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, AMPA; RECEPTORS, KAINIC ACID; SEIZURES;

EID: 0032718907     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991086d     Document Type: Article

References (36)

1. (a) Ikonomidou, C.; Turski, L. Glutamate in Neurodegenerative Disorders. In CNS Neurotransmitters and Neuromodulators: Glutamate; Stone, T. W., Ed.; CRC Press: New York, 1995; pp 253-266. (b) Danysz, W.; Pearsons, C. G.; Bresink, I.; Quack, G. Glutamate in CNS Disorders. Drug News Perspect. 1995, 8, 261-277.
2. (a) Ikonomidou, C.; Turski, L. Glutamate in Neurodegenerative Disorders. In CNS Neurotransmitters and Neuromodulators: Glutamate; Stone, T. W., Ed.; CRC Press: New York, 1995; pp 253-266. (b) Danysz, W.; Pearsons, C. G.; Bresink, I.; Quack, G. Glutamate in CNS Disorders. Drug News Perspect. 1995, 8, 261-277.
3. (a) Donevan, S. D.; Rogawski, M. A. GYKI 52466, a 2,3-Benzodiazepine, is a Highly Selective, Noncompetitive Antagonist of AMPA/Kainate Receptor Responses. Neuron 1993, 10, 51-59. (b) Rogawski, M. A. Therapeutic Potential of Excitatory Amino Acid Antagonists: Channel Blockers and 2,3-Benzodiazepines. Trends Pharmacol. Sci. 1993, 14, 325-331.
4. (a) Donevan, S. D.; Rogawski, M. A. GYKI 52466, a 2,3-Benzodiazepine, is a Highly Selective, Noncompetitive Antagonist of AMPA/Kainate Receptor Responses. Neuron 1993, 10, 51-59. (b) Rogawski, M. A. Therapeutic Potential of Excitatory Amino Acid Antagonists: Channel Blockers and 2,3-Benzodiazepines. Trends Pharmacol. Sci. 1993, 14, 325-331.
5. (a) Chapman, A. G.; Smith, S. E.; Meldrum, B. S. The Anticonvulsant Effect of the Non-NMDA Antagonists, NBQX and GYKI 52466, in Mice. Epilepsy Res. 1991, 9, 92-96.
6. (b) Smith, S. E.; Durmuller, N.; Meldrum, B. S. The non-N-methyl-D-aspartate Receptor Antagonists, GYKI 52466 and NBQX are Anticonvulsant in two Animal Models of Reflex Epilepsy. Eur. J. Pharmacol. 1991, 201, 179-183.
7. (a) Smith, S. E.; Meldrum, B. S. Cerebroprotective Effect of a Non-N-Methyl-D-Aspartate Antagonist, GYKI 52466, After Focal Ischemia in the Rat. Stroke 1992, 23, 861-864.
8. (b) Arvin, B.; Lekieffre, D.; Graham, J. L.; Moncada, C.; Chapman, A. G.; Meldrum, B. S. Effect of the Non-NMDA Receptor Antagonist GYKI 52466 on the Microdialyzate and Tissue Concentrations of Amino Acids Following Transient Forebrain Ischemia. J. Neurochem. 1994, 62, 1458-1467.
9. Tarnawa, I.; Berzsenyi, P.; Andrasi, F.; Botka, P.; Hamori, T.; Ling, I.; Körösi, J. Structure-Activity Relationships of 2,3-Benzodiazepine Compounds with Glutamate Antagonistic Action. Bioorg. Med. Chem. Lett. 1993, 3, 99-104.
10. Donevan, S. D.; Yamaguchi, S. I.; Rogawski, M. A. Non-N-methyl-D-aspartate Receptor Antagonism by 3-N-Substituted 2,3-Benzodiazepines: Relationship to Anticonvulsant Activity. J. Pharmacol. Exp. Ther. 1994, 271, 25-29.
11. De Sarro, G.; Chimirri, A.; De Sarro, A.; Gitto, R.; Grasso, S.; Giusti, P.; Chapman, A. G. GYKI 52466 and Related 2,3-Benzodiazepines as Anticonvulsant Agents in DBA/2 Mice. Eur. J. Pharmacol. 1995, 294, 411-422.
12. Chimirri, A.; De Sarro, G.; De Sarro, A.; Gitto, R.; Grasso, S.; Quartarone, S.; Zappalà, M.; Giusti, P.; Libri, V.; Constanti, A.; Chapman, A. G. 1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: Novel AMPA Receptor Antagonists. J. Med. Chem. 1997, 40, 1258-1269.
13. (a) De Sarro, A.; De Sarro, G.; Gitto, R.; Grasso, S.; Micale, N.; Quartarone, S.; Zappalà, M. 7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as Novel AMPA Receptor Antagonists. Bioorg. Med. Chem. Lett. 1998, 8, 971-976.
14. (b) De Sarro, A.; De Sarro, G.; Gitto, R.; Grasso, S.; Micale, N.; Zappalà, M. Synthesis and Anticonvulsant Activity of New 2,3-Benzodiazepines as AMPA Receptor Antagonists. Farmaco 1999, 54, 179-189.
15. Chimirri, A.; De Sarro, G.; De Sarro, A.; Gitto, R.; Quartarone, S.; Zappalà, M.; Constanti, A.; Libri, V. 3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: A New Class of AMPA Receptor Antagonists. J. Med. Chem. 1998, 41, 3409-3416.
16. (a) Chapman, A. G.; Croucher, M. J.; Meldrum, B. S. Evaluation of Anticonvulsant Drugs in DBA/2 Mice with Sound-Induced Seizures. Arzneim. Forsch. 1984, 34, 1261-1264. (b) Engstrom, F. L.; Woodbury, D. M. Seizure Susceptibility in DBA/2 and C57 Mice: the Effects of Various Convulsants. Epilepsia 1988, 29, 389-395.
17. (a) Chapman, A. G.; Croucher, M. J.; Meldrum, B. S. Evaluation of Anticonvulsant Drugs in DBA/2 Mice with Sound-Induced Seizures. Arzneim. Forsch. 1984, 34, 1261-1264. (b) Engstrom, F. L.; Woodbury, D. M. Seizure Susceptibility in DBA/2 and C57 Mice: the Effects of Various Convulsants. Epilepsia 1988, 29, 389-395.
18. Ito, I.; Tanabe, S.; Kohda, A.; Sugiyama, H. Allosteric Potentiation of Quisqualate Receptors by Nootropic Drug Aniracetam. J. Physiol. (London) 1990, 424, 533-543.
19. Venkov, A. P.; Ivanov, I. I. Synthesis of 3-Oxo-2,3-Dihydroisoquinolines from Ethyl 2-Acylphenylacetates and Formamides. Synth. Commun. 1994, 24, 1145-1150.
20. Pellettier, J. C.; Hesson, D. P.; Jones, K. A.; Costa, A. M. Substituted 1,2-Dihydrophthalazines: Potent, Selective, and Noncompetitive Inhibitors of the AMPA Receptor. J. Med. Chem. 1996, 39, 343-346.
21. Johansen, T. H.; Chaudhary, A.; Verdoorn, T. Interactions among GYKI-52466, cyclothiazide, and Aniracetam at recombinant AMPA and Kainate receptors. Mol. Pharmacol. 1995, 48, 946-955.
22. (a) Bliss, T. V. P.; Collingridge, G. L. A Synaptic Model of Memory: Long-Term Potentiation in the Hippocampus. Nature 1993, 361, 31-39. (b) Paternain, A. V.; Morales, M.; Lerma, J. Selective Antagonism of AMPA Receptors Unmasks Kainate Receptor-Mediate Responses in Hippocampal Neurones. Neuron 1995, 14, 185-189.
23. (a) Bliss, T. V. P.; Collingridge, G. L. A Synaptic Model of Memory: Long-Term Potentiation in the Hippocampus. Nature 1993, 361, 31-39. (b) Paternain, A. V.; Morales, M.; Lerma, J. Selective Antagonism of AMPA Receptors Unmasks Kainate Receptor-Mediate Responses in Hippocampal Neurones. Neuron 1995, 14, 185-189.
24. (a) Boyce, C. B. C.; Milborrow, B. V. A Simple Assessment of Partition Data for Correlating Structure and Biological Activity Using Thin-Layer Chromatography. Nature 1965, 208, 537-539. (b) Pietrogrande, M. C.; Borea, P. A.; Biagi, G. L. Lipophilicity Measurements of Benzodiazepine-Receptor Ligands by Reversed-Phase Liquid Chromatography. Comparison between High-Performance Liquid and Thin-Layer Chromatography. J. Chromatogr. 1988, 447, 404-409.
25. (a) Boyce, C. B. C.; Milborrow, B. V. A Simple Assessment of Partition Data for Correlating Structure and Biological Activity Using Thin-Layer Chromatography. Nature 1965, 208, 537-539. (b) Pietrogrande, M. C.; Borea, P. A.; Biagi, G. L. Lipophilicity Measurements of Benzodiazepine-Receptor Ligands by Reversed-Phase Liquid Chromatography. Comparison between High-Performance Liquid and Thin-Layer Chromatography. J. Chromatogr. 1988, 447, 404-409.
26. Collins, R. L. Audiogenic Seizures. In Experimental Models of Epilepsy; Purpura, P., Penry, J. K., Tower, D., Woodbury, D. M., Walter, R., Eds.; Raven Press: New York, 1972; pp 347-372.
27. De Sarro, G. B.; Croucher, M. J.; Meldrum, B. S. Anticonvulsant Actions of DS 103-282: Pharmacological Studies in Rodents and the Baboon Papio papio. Neuropharmacology 1984, 23, 526-530.
28. Swinyard, E. A.; Brown, W. C.; Goodman, L. S. Comparative Assays of Antiepileptic in Mice and Rats. J. Pharmacol. Exp. Ther. 1952, 106, 319-330.
29. Swinyard, E. A.; Woodhead, J. M. Experimental Detection, Quantification and Evaluation of Anticonvulsants. In Epileptic Drugs; Woodbury, D. M., Penry, J. K., Pippenger, C. E., Eds.; Raven Press: New York, 1982; pp 111-126.
30. De Sarro, G. B.; Ongini, E.; Bertorelli, R.; Aguglia, U.; De Sarro, A. Excitatory Amino Acid Neurotransmission through both NMDA and Non-NMDA Receptors is Involved in the Anti-convulsant Activity of Felbamate in DBA/2 mice. Eur. J. Pharmacol. 1994, 262, 11-19.
31. Gallo, V.; Ciotti, M. T.; Coletti, A.; Aloisi, F.; Levi, G. Selective release of glutamate from cerebellar granule cells differentiating in culture. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 7919-7923.
32. Hamil, O. P.; Marty, A.; Neher, E.; Sakmann, B.; Sigworth, F. J. Improved patch clamp techniques for high-resolution current recording from cells and free-membrane patches. Pflugers Arch. 1981, 474, 85-100.
33. Murase, K.; Ryu, P. D.; Randic, M. Excitatory and inhibiting amino acids and peptide-induced responses in acutely isolated rat spinal horn neurons. Neurosci. Lett. 1989, 103, 56-63.
34. Dunham, N. W.; Miya, T. S. A Note on a Simple Apparatus for Detecting Neurological Deficit in Rats and Mice. J. Am. Pharm. Assoc. 1967, 46, 208-209.
35. Litchfield, J.; Wilcoxon, F. A Simplified Method of Evaluating Dose-Effect Experiments. J. Pharmacol. Exp. Ther. 1949, 96, 99-113.
36. McPherson, G. I. Ligand, release 2.0; Elsevier Biosoft: Cambridge, 1987.